Photos: Chicago

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ICY WINDS WHIPPING off the lake, mirrored towers stretching up into the heavens and politics as colorful as its lake shores are pure: Chicago remains the most modern, and the most "American," of our big cities, as vast and variegated as the country that spawned it.

The birthplace of the skyscraper—nowhere showcased to such effect as in the vertiginous skyline of the Loop—still has the biggest shoulders of any great American city. But beyond the vertical ambition of downtown is another Chicago, a metropolis where for almost two centuries people from all over the world—from Poland, Italy, Ireland, and now Mexico, Bosnia and Iraq—have migrated to nab their nugget of the American Dream.

In the low-slung streets of Lakeview and Lincoln Park, Chicagoans indulge the sensual pleasures that keep them warm all interminable winter long: deep-dish pizza and Vienna Beef hot dogs and the reddest slabs of meat, anywhere and always. Sports are serious business here, and comedy (hence, Second City and lesser-known troupes too), and not least of all music: Where would we be without Chicago blues, house music and that uniquely Midwestern brand of indie rock?

From the steakhouses of the so-called Viagra Triangle to the hipster corridors of Wicker Park, Chi-town (they said it, we didn't) has come a long way since the days of Prohibition and Al Capone–fueled street-corner dramas, but it's never shed that frontier edginess. All and all, not bad for "flyover country."

—Laura Moser

The Restaurateur: Grant Achatz

Chef/owner of Alinea and soon-to-open restaurants Next and Aviary; named James Beard "Outstanding Chef" in 2008

Late-Night Spot // The Drawing Room. This subterranean cocktail lounge turns out imaginative elixirs. Open until 4 a.m. on Saturdays, it's one of the few options for quality late-night fare like bacon-wrapped pork belly and fried avocados. 937 North Rush St., thedrchicago.com

Tasty Raps // Schwa. This Wicker Park foodie gem is all about Michael Carlson, voted a "Best New Chef" by Food & Wine in 2006. Nine-course meals served over the world kitchen's rap-metal soundtrack—the best "tasting menu" in the city. 1466 N. Ashland Ave., schwarestaurant.com

Playing Grounds // Grant Park. This amazing acreage hosts music fests, innovative plays…and presidential acceptance speeches watched by 100,000 attendees. It's also home to Millennium Park, the Art Institute, the Field Museum of Natural History and the Shedd Aquarium. Since 1835, the park-of-parks abides. chicagoparkdistrict.com

Strike a Pose // Ten Pin. Chicagoans live hard and bowl harder, but this is the top lane for diehards and recreationalists. Order a shot of milk (with chocolate chip-toffee cookies) or a "10pintini"—no one will judge. 330 N. State St., 10pinchicago.com

Place to Meat // The Chicago Chop House. The Bentley of steakhouses in a city known for them, this bloody good politico holdout, situated in a century-old Victorian, features a 64-ounce porterhouse steak and dozens of wines by the glass. 60 W. Ontario St., chicagochophouse.com

The Design Guy: Nate Berkus

Designer; host of "The Nate Berkus Show"; Chicago resident since the early 1990s

ENLARGE

Nate Berkus

Bargain Hunting // The Randolph Street Market Festival. For me, trawling for finds here is the definition of a perfect weekend morning. You can land distinct antiques, great vintage estate jewelry and cool designer pieces. It's open Nov. 20-21, and then one weekend a month from May through September. 1350 block of W. Randolph St., randolphstreetmarket.com

Drive-In // Superdawg. Whenever I get back to Chicago, I go directly to this iconic hot dog heaven for a taste of my hometown. 6363 N. Milwaukee Ave., superdawg.com

Killer Karaoke // Blue Frog Bar & Grill. There are many karaoke bars in Chicago, but this River North spot is the most fun (and supportive) watering hole to belt it out. I'm just glad none of my awful Madonna renditions have made it onto YouTube…yet. 676 N. La Salle St., 312-943-8900

Shopping Spree // Broadway Antique Market and the Edgewater Antique Mall. Both vintage treasure troves are within a few blocks of each other on the North Side. 6130 N. Broadway, bamchicago.com; 6314 N. Broadway, edgewaterantiquemall.com

International Velvets // Pavilion. This place has a wonderful selection of 20th-century decorative arts and furnishings from France, Italy and Scandinavia. 2055 N. Damen Ave., pavilionantiques.com

Three For the Road // Green Zebra, The Violet Hour and Rosa's Lounge. Start at the Zebra, for its vegan cuisine, in Wicker Park; then head to the so-chic Violet Hour, in Bucktown, for perfect martinis; and wrap it up with live blues at Rosa's. 1460 W. Chicago Ave., greenzebrachicago.com; 1520 N. Damen Ave., theviolethour.com; 3420 W. Armitage Ave., rosaslounge.com

Midcentury Now // Wright. I love browsing the showroom and watching the bidders at this important auction house. The auctions range from shows selling modern Eames chairs and Scandinavian furniture to canvases by George Condo and Kenny Scharf. 1440 W. Hubbard St., wright20.com

Corrections & Amplifications Nate Berkus is a decorator whose television program, "The Nate Berkus Show," airs in syndication nationally. An earlier version of this article incorrectly called Mr. Berkus an interior designer, a classification that requires professional licensing, and said his show aired only on NBC.

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